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Webb was born in St. Joseph, Missouri, to James Henry Webb Sr., and his wife, Vera Lorraine (Hodges).[3] The second of four children and the older son, he grew up in a military family, moving frequently as his father's career in the United States Air Force required. The family crisscrossed the country, living in Missouri, Illinois, Texas, Alabama, Nebraska, California, and Virginia, as well as in England, where his father was an exchange officer with the Royal Air Force.[4] His father flew B-17s and B-29s during World War II, and flew Air Force cargo aircraft during the 1948-49 Berlin airlift. After developing an inner ear disorder, Meniere's Disease, he became a pioneer in the Air Force missile program, later serving as the commanding officer of the 1001st Missile Squadron at Vandenberg Air Force Base. Webb's parents are buried at the Arlington National Cemetery.

Webb attended more than a dozen schools across the U.S. and in England. After graduating from high school in Bellevue, Nebraska, he attended the University of Southern California on a Naval Reserve Officers Training Corps scholarship from 1963 to 1964[6] (and is a member of Delta Chi).[7] In 1964, Webb earned appointment to the United States Naval Academy in Annapolis, Maryland. At Annapolis, Webb was a member of the Brigade Honor Committee and the Brigade Staff. When he graduated in 1968,[8] he received the Superintendent's Letter for Outstanding Leadership.[9] After his medical retirement from the Marine Corps due to injuries received in Vietnam, Webb enrolled in law school at Georgetown University where he earned a Juris Doctor and received the Horan Award for excellence in legal writing.[8]

Webb is married to Hong Le Webb, a Vietnamese-American securities and corporate lawyer for Murphy and McGonigle[10]. Hong Le was born in South Vietnam and came to the United States when she was seven, after the fall of Saigon. She grew up in New Orleans, Louisiana. They married in October 2005.[11] Webb was married twice previously, and has four grown children. Hong Le and Jim Webb have one child together, Georgia LeAnh, born December 2006. Webb is also a stepfather to Hong Le's daughter from a previous marriage.[12] Jim Webb speaks Vietnamese.[13]

Webb received the Navy Cross for actions on July 10, 1969. The citation read:

The Navy Cross is presented to James H. Webb, Jr., First Lieutenant, U.S. Marine Corps, for extraordinary heroism while serving as a Platoon Commander with Company D, First Battalion, Fifth Marines, First Marine Division (Reinforced), Fleet Marine Force, in connection with combat operations against the enemy in the Republic of Vietnam. On July 10, 1969, while participating in a company-sized search and destroy operation deep in hostile territory, First Lieutenant Webb's platoon discovered a well-camouflaged bunker complex that appeared to be unoccupied. Deploying his men into defensive positions, First Lieutenant Webb was advancing to the first bunker when three enemy soldiers armed with hand grenades jumped out. Reacting instantly, he grabbed the closest man and, brandishing his .45 caliber pistol at the others, apprehended all three of the soldiers. Accompanied by one of his men, he then approached the second bunker and called for the enemy to surrender. When the hostile soldiers failed to answer him and threw a grenade that detonated dangerously close to him, First Lieutenant Webb detonated a claymore mine in the bunker aperture, accounting for two enemy casualties and disclosing the entrance to a tunnel. Despite the smoke and debris from the explosion and the possibility of enemy soldiers hiding in the tunnel, he then conducted a thorough search that yielded several items of equipment and numerous documents containing valuable intelligence data. Continuing the assault, he approached a third bunker and was preparing to fire into it when the enemy threw another grenade. Observing the grenade land dangerously close to his companion, First Lieutenant Webb simultaneously fired his weapon at the enemy, pushed the Marine away from the grenade, and shielded him from the explosion with his own body. Although sustaining painful fragmentation wounds from the explosion, he managed to throw a grenade into the aperture and completely destroy the remaining bunker. By his courage, aggressive leadership, and selfless devotion to duty, First Lieutenant Webb upheld the highest traditions of the Marine Corps and of the United States Naval Service.[19]

In the October 13, 2015 CNN Democratic Debate, when asked, "Which enemy are you most proud of?", Webb stated, "I'd have to say, the enemy soldier that threw the grenade that wounded me, but he's not around right now to talk to."[20]

In a November 19, 2006 appearance on Meet the Press, Webb told host Tim Russert, "I'm one of these people who – there aren't many of us – who can still justify for you the reasons that we went into Vietnam, however screwed up the strategy got."[21]

From 1977 to 1981, Webb worked on the staff of the House Committee on Veterans Affairs. During this time, he also represented veterans pro-bono. Webb taught at the Naval Academy and was criticized for a 1979 article published in Washingtonian magazine, titled "Women Can't Fight"[23] (see "2006 Senate campaign" below). He attended the 1980 Republican National Convention in Detroit and led the Pledge of Allegiance in the opening session.[24]

In a 1990 New York Times opinion piece, Webb opposed further U.S. military escalation in Saudi Arabia during Operation Desert Shield citing lack of a coherent strategy and consent from the United States Congress. He also warned against a permanent military presence in the Middle East.[27] Seven months before the beginning of the 2003 Iraq War, Webb wrote an essay for The Washington Post in which he

questioned whether an overthrow of Saddam would "actually increase our ability to win the war against international terrorism" and pointed out that the measure of military success can be preventing wars as well as fighting them. He charged, "those who are pushing for a unilateral war in Iraq know full well that there is no exit strategy if we invade." He concluded, "the Iraqis are a multiethnic people filled with competing factions who in many cases would view a U.S. occupation as infidels invading the cradle of Islam.... In Japan, American occupation forces quickly became 50,000 friends. In Iraq, they would quickly become 50,000 terrorist targets."[28]

In the Democratic primary on June 13, 2006, Webb faced longtime businessman and lobbyist Harris Miller. Webb won with 53.5% of the vote, in a race with low turnout.[33]

On August 11, 2006, an incident occurred in which Allen used the word macaca to refer to S.R. Sidarth, who was filming an event as a "tracker" for the Webb campaign. A poll the following week showed Webb gaining 10 percentage points. The race, which at one point looked like a sure win for Allen, became one of the most watched and closest races of the 2006 elections. Webb's entry into the race and primary victory changed the political landscape. Political analyst Larry Sabato said in May that "Jim Webb is George Allen's worst nightmare: a war hero and a Reagan appointee who holds moderate positions.... Allen tries to project a Reagan aura, but Webb already has it."[34]

On September 7, 2006, Webb released his first television advertisement, which included footage of a 1985 speech by Ronald Reagan that praised Webb's service as a Marine.[35] The next day, the Chief of Staff for the Reagan Library wrote Webb's campaign on behalf of former first lady Nancy Reagan, urging them not to air the advertisement saying it was neither fair nor respectful because it gave the impression of an endorsement.[36][37] The Webb campaign disagreed, saying, "What Reagan said about Jim Webb, that belongs to Jim Webb, frankly."[36] The library said they ask all candidates to refrain from using the former president's image but declined to say if they would request the Allen campaign to remove the image of Reagan used on his campaign website.[36]

Five female graduates of the United States Naval Academy held a press conference, decrying Webb's 1979 article, "Women Can't Fight." The women said Webb's article contributed to an atmosphere of hostility and harassment towards women at the academy. Webb was later endorsed by nine military women who stated that Webb is a "man of integrity" who "recognizes the crucial role that women have in the military today."[38]

In October 2006, the Allen campaign issued a press release quoting several passages from Webb's novels with sexual content, including graphic references to female anatomy and purported pedophilia, homosexuality and incest, citing a passage in which a Southeast Asian father ritually places the penis of his young son in his mouth. The press release said that the passages showed a "continued pattern of demeaning women".[39] Allen's campaign refused to tell a local radio news station, WTOP-FM, whether it in fact had issued a news release on the matter.

In response, Jim Webb explained to The Washington Post, "I actually saw this happen in a slum in Bangkok when I was there as a journalist."[40] According to an article on Raw Story, the conservative website CNS News cited a case in Nevada in which a Cambodian mother was arrested for a similar act. According to the CNS article, an office manager for the Cambodian Association of America confirmed it is a cultural norm in Thailand and Cambodia.[41]

On November 9, 2006, after AP and Reuters projected that Webb had won the seat, Allen conceded the election. Although the margin was narrow – less than half of 1% of the total vote and therefore small enough under Virginia law to allow demanding a recount – Allen stated that he would not challenge the result.[citation needed]

"That same day, an op-ed authored by Webb appeared in the pages of The Wall Street Journal. Titled 'Class Struggle: American workers have a chance to be heard'. The piece addressed the harmful economic inequality in the U.S., with the elites on one side and American workers on the other side. The article cites the "age of globalization and outsourcing, and with a vast underground labor pool from illegal immigration", as well as extravagant executive compensation, the detrimental effects of free trade and globalization, iniquitous tax cuts, speedily rising health care costs, and stagnation in income as the reasons for the increasing disparity between the elites and American workers.[43]

On November 28, 2006, at a White House reception for those newly elected to Congress, Webb did not choose to wait in the line to have his picture taken with the president,[44] whom Webb often criticized during the campaign. The president approached Webb later and asked him, "How's your boy?", referring to Webb's son, a Marine serving in Iraq. Webb replied "I'd like to get them out of Iraq, Mr. President." Bush responded, "That's not what I asked you. How's your boy?", Webb responded, "That's between me and my boy, Mr. President." The Hill cited an anonymous source who claimed that Webb was so angered by the exchange that he confessed he was tempted to "slug" the president.[45] Webb later remarked in an interview, "I'm not particularly interested in having a picture of me and George W. Bush on my wall."[46]

In response to the incident, some conservatives criticized Webb, including George Will, who called Webb a "boor" and wrote, "[Webb] already has become what Washington did not need another of, a subtraction from the city's civility and clear speaking."[47][48] Others, such as conservative columnist and former Reagan speechwriter Peggy Noonan, reserved their criticism for Bush, writing: "I thought it had the sound of the rattling little aggressions of our day, but not on Mr. Webb's side."[49]

My feeling about that – first of all, it's been kind of a bit overblown. But I think when people are now seeing how John McCain is handling the situation with his son being in the Marine Corps, perhaps they can understand a little bit more what I was having to go through during the entire campaign. I greatly respect my son's service and all of the people who are serving. At the same time, I have not commented, even to many of my friends, about the operational side. That's personal to me in terms of my feelings about it. And it was not a casual comment. As I said in the piece that you just ran, I think the best article that was written on that was by Peggy Noonan in The Wall Street Journal when she basically said that the lack of civility was not mine and I feel that way.[50]

After his son returned from Iraq, Webb "buried the hatchet" with the president by setting up a private chat with his son, the president, and himself in the Oval Office.[51]

On January 4, 2007, Webb was sworn into the 110th U.S. Senate, accompanied by Sen. John Warner, R-Va., a fellow former Secretary of the Navy; and former Virginia Democratic Sen. Chuck Robb, who held the same seat before losing to Allen.
On his first day in the Senate, Webb introduced the Post-9/11 Veterans Educational Assistance Act, to expand benefits for military families, which he had written. The act replaces key provisions of the Montgomery G.I. Bill for recent veterans and "makes veterans benefits identical to those soldiers received following World War II". "With many of our military members serving two or three tours of duty in Iraq and Afghanistan, it is past time to enact a new veterans' education program modeled on the World War II era G.I. bill. This is exactly what our legislation does", Webb said. It became law on June 30, 2008, as part of the Supplemental Appropriations Act of 2008.[52]

What we really need to do is to get into the arena where we can talk about a strategy, talk about the pluses and the minuses of the Baker-Hamilton Commission and work toward a solution that, on the one hand, will allow us to remove our combat troops, but on the other, will increase the stability of the region, allow us to continue to fight against international terrorism and allow us, as a nation, to address our strategic interests around the world. And this is – this is one of the drawbacks that we've had with so many troops having been put into this constant rotational basis inside one country when we have a war against international terrorism that's global.[citation needed]

I – you know, I lived through Vietnam. I lived through it as a Marine and I know that those sorts of approaches, while they seem attractive on one level are really not that realistic. What we want to do – and I was talking with a number of senators today – is to try to get some of these so-called emergency legislation packages back into the committee process so that the committees can actually play.[53]

On January 23, 2007, Webb delivered the Democratic response to the President's State of the Union address, focusing on the economy and Iraq.[54] Webb's speech drew positive reviews, and was regarded as one of the stronger State of the Union responses in recent memory.[55]

On March 5, 2007, Webb introduced his second piece of legislation, S. 759, intended to prohibit the use of funds for military operations in Iran without the prior approval of Congress. In a statement on the floor of the Senate, Webb said, "The major function of this legislation is to prevent this Administration from commencing unprovoked military activities against Iran without the approval of the Congress. The legislation accomplishes this goal through the proper constitutional process of prohibiting all funding for such an endeavor."[56]

On March 26, 2007, a senatorial aide of Webb, Phillip Thompson, was arrested for carrying Webb's loaded pistol as he entered the Russell Senate Office Building and for carrying unregistered ammunition. The weapon was discovered when Thompson went through an X-ray machine with a briefcase that contained a loaded pistol and two additional loaded magazines.[57] Charges against the aide were dismissed after prosecutors concluded it could not be proved beyond a reasonable doubt that Thompson was aware that the gun and ammunition were in the briefcase.[58] Webb responded to his aide's arrest by reiterating his support for gun-owners' rights:

I'm a strong supporter of the Second Amendment; I have had a permit to carry a weapon in Virginia for a long time; I believe that it's important; it's important to me personally and to a lot of people in the situation that I'm in to be able to defend myself and my family.[59]

On August 14, 2009, Webb visited Myanmar (Burma), seeing its junta's leader, Gen. Than Shwe, and also the pro-democracy leader Aung San Suu Kyi, who was under house arrest. During Webb's visit with Than Shwe, Webb negotiated the release and deportation of an imprisoned American, John Yettaw.[60][61] Upon his return to the U.S., Webb wrote an editorial titled "We Can't Afford to Ignore Myanmar" for The New York Times, arguing for the easing of sanctions on the country. Webb stated that sanctions have isolated the country, thereby encouraging the ruling regime to turn to China and allowing "China to dramatically increase its economic and political influence in Myanmar, furthering a dangerous strategic imbalance in the region." Webb also noted that, unlike Myanmar, China does not allow opposition parties.[62] Webb has stated that he started the pivot to Asia during the Bush Administration.[63]

Webb visited Vietnam as part of a two-week trip to five Southeast Asian countries. Webb, who can speak Vietnamese, has had a continuous involvement in Asian and Pacific affairs that long predates his time in the Senate. In addition to his more recent visits as a member of the Senate Foreign Relations Committee, Webb has worked and traveled throughout this vast region, from Micronesia to Burma, for nearly four decades, as a Marine Corps officer, a defense planner, a journalist, a novelist, a Department of Defense executive, and as a business consultant. He worked in the 1990s as a consultant for companies attempting to do business in Vietnam.[64]

On March 26, 2009, Webb filed the Criminal Justice Commission Act of 2009 (SB 714), which would create a blue ribbon commission to reevaluate the criminal justice system and drug policy and make recommendations for reform.[65] Noting that the United States houses 25% of the world's inmates despite having only 5% of the world's population, Webb proposed a comparison between U.S. incarceration policies and those of other developed nations.[66] At a United States Senate Judiciary Subcommittee on Crime and Drugs hearing, Webb described the criminal justice system as being in "... a profound, deeply corrosive crisis that we have largely been ignoring at our peril." He also criticized the lack of standards in prison administration and highlighted the justice system's negative impact on communities. The subcommittee chairman, Sen. Arlen Specter (D-PA), expressed support for the bill at the hearing and indicated his intent to move the bill to the full United States Senate Committee on the Judiciary.[67] By the end of June 2010, the bill had 39 cosponsors.[68]

In the fall of 2009, an amendment to SB 714 was proposed by Sen. Charles Grassley (R-IA) that would have prohibited the commission created by the bill from discussing or recommending the decriminalization or legalization of any substance prohibited under the Controlled Substances Act.[69] The proposed amendment drew criticism from some in the online community. Grassley later rescinded the amendment and claimed in a Des Moines Register op-ed that he had proposed it to "start a debate on this important issue".[70] SB 714 passed the Senate Judiciary Committee by a voice vote on January 21, 2010.[citation needed]

Webb was frequently mentioned as a possible vice presidential Democratic nominee for Barack Obama in 2008 due to his military experience and moderate policy positions.[73][74][75][76][77] Although he said he was not interested in the vice presidency,[78] speculations about his being picked by Obama, the presumptive Democratic nominee at the time, were still heard.[75]

On July 7, Webb effectively removed himself as a possible candidate for Vice President in a statement made to Time, stating that he intended to serve his term in the Senate and "under no circumstances will I be a candidate for Vice President."[79] Obama went on to choose fellow senator Joe Biden as his running mate.

On June 15, 2015, Webb announced he would make a decision regarding a presidential bid by the end of the month.[83]
Webb made a formal announcement on July 2, 2015, through an open letter on his webb2016 website, that he would seek the Democratic Party's nomination for the presidency.[84]

On October 20, 2015, after failing to gain substantial support for his campaign ahead of the primaries, Webb announced that he would be dropping out of the Democratic presidential race in favor of a possible independent presidential run citing his "frustration with party leadership".[85] On February 11, 2016, he ruled out making an independent presidential bid.[86]

On March 4, 2016, Webb stated that he would not vote for Hillary Clinton in the 2016 presidential election and declined to rule out voting for Donald Trump.[87]

Webb's successful first novel, Fields of Fire (1978), drawn from personal experience, tells the story of a platoon of United States Marines in late 1960s Vietnam. Reviewers hailed its descriptions of infantry life and combat.[88][89][90]

After five more novels, he wrote Born Fighting: How the Scots-Irish Shaped America (2004), a personal view of Scots-Irish and their place in American history and culture.

Warner Brothers acquired Webb's script for Whiskey River.[92] The script concerns an American soldier who is injured in Iraq and returns to the United States. Before completing rehabilitation, he is called back to active duty. His father, in an attempt to save his son's life, kidnaps him.[92]

In October 2006, while commenting on the need to break away from stereotypical movie villains, Webb stated, "[e]very movie needs a villain. Towel-heads and rednecks—of which I am one ... became the easy villains in so many movies out there."[93]

Webb is a prolific writer and has written for many national journals including the Marine Corps Gazette, Proceedings of the United States Naval Institute, USA Today, The New York Times, The Washington Post, and The Wall Street Journal.[94]